Deprotonation of Lithiated Benzenes
- 25 February 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (6) , 2111-2122
- https://doi.org/10.1021/jo035265l
Abstract
The deprotonation energies of all possible lithiobenzenes (C6LinH6-n, n = 0−5) were computed at B3LYP/6-311+G(d,p). Based on natural population analysis, the conjugate bases can be thought of as salts between a polyanionic phenyl core and associated lithium cations. The most stable structures maximize the electrostatic attraction between these two species, typically by positioning the lithium cations to bridge in the ring plane across two adjacent carbanion centers. Favorable deprotonation occurs when the formal carbanion centers are adjacent to each other and then the proton is removed from an adjacent carbon. The deprotonation free energies range from 365.0 to 397.2 kcal mol-1, with most of them less than the deprotonation free energy of benzene (391.8 kcal mol-1).Keywords
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